This part is rated R for explicit sexual content, so yeah .. you've been warned!
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Stiles eyes popped open almost as fast as he had closed them, and as Derek climbed up onto the table again, it creaked under him. The heavy weight of Derek’s cock could be felt through the denim and the heat was making Stiles head spin a little. Soon the alpha was over top of him, body glistening already with a thin sheen of sweat even though they hadn’t done anything yet. Stiles was burning up, and his breathing was still rough and ragged.
Derek straddled one of Stiles legs and for a quick moment he ground down deliberately against his thigh. Even without skin-on-skin contact Stiles was seeing stars. His eyes were scrunched tightly again. The elder male pressed down harder and smiled when immediately, like the after effects of pushing a button, the teen’s eyes shot open. They were wide almost as if he were just electrocuted.
“Spread ‘em,” said Derek.
“Okay,” Stiles replied weakly, and obeyed. He hardly recognized his own voice. He spread his legs just wide enough so that Derek could fit both knees on the space in between them if he really wanted to, but the latter made no effort to move. Instead he looked down at Stiles through piercing green, locking their eyes.
“More, Stiles.” The wolf got up on all four, both hands on either side of the young man’s head. His nails scratched against the surface, and Stiles wondered for a brief second when exactly they had come out. His face was still very much Derek, but the rest of his body was reacting differently to the situation.
Lifting one hand, Derek dipped his fingers carefully under Stiles thigh, the one not trapped between his own, and pulled it up and over off the table so it was folded more to his chest and angled away from them. Stiles would have felt very exposed if he didn’t still have his jeans on, but there was nothing he wanted more than to remove them in this moment. He waited for Derek to finish demonstrating what he ought to do with his long limbs then nodded.
Before rolling off to the side on the rather large table, Derek’s hands found Stiles hips. He smiled as his fingers dipped below the waistband by the belt loops, and Stiles winced at the faint scratching of nails against his sensitive skin. Without warning Derek pulled the tough material down, and dragging against the tabletop the action brought his boxer-shorts with them. He was grateful that today he had settled for a plain pair rather than the limited edition Spidey ones he had planned to don to school this morning.
Stiles hissed lightly at the drag of jean on his cock but then let out a exhalation of absolute relief when his member hit the cool air, standing at attention just inches away from where Derek had stopped pulling at the fabric. Derek eased off of the nervous male, his own dick shaking about obscenely with every movement to which Stiles eyes followed every sway and slice. The air was thick with need and whilst some of it came off the elder male, Stiles knew he was the culprit for the vast majority.
Derek’s dick rested for a second on his stomach as he lay on his side, his elbow propping him up and one leg bent, showcasing his impressive length, to watch Stiles push his pants to the floor. They were both painfully hard, but Stiles had his age and lack of previous sexual encounters to blame for that. What was Derek’s excuse?
Stiles brain wouldn’t let him believe it possible that Derek could actually like him, not to mention be turned on by him.
When he had finished removing his pants, they fell to a messy pile on the floor. Derek watched them fall, reminding the teen of a cat zeroing in on a bug on the wall, making sure it didn’t come any closer than it was wanted, then he threw himself over Stiles in one fluid movement. He was heavy, yes, but with surprising control for someone not exactly operating on all …upstairs cylinders. Derek’s biceps strained visible as he tried to settle down gently rather than crash their pelvises together. His brow was furrowed, and there were deep crinkles in between them, so Stiles knew it was taking a lot of effort.
“You’re not going to break me, big guy,” he said as calmly as he could, but his voice was wavering. His nerves were getting the better of him and it most certainly showed even more obviously than Derek’s struggles at restraint. The alpha’s dick hitting his lower abdomen as the male finally nestled his body comfortably onto Stiles, drew out a loud moan. His cheeks turned immediately red when Stiles made the connection in his mind that it sounded an awful lot like one of the adult stars in a film he’d watched earlier. What was most embarrassing was that guy was getting rammed, and all they were doing was touching.
Derek began to move slowly, grinding down with more pressure each time as Stiles moans grew more audible as a sign he was certainly liking this rhythm. Going down so his forearms were flat, further down against the table from Stiles arms, which were stretched out over his head, Derek tucked them under the young male’s own arms. Gripping his shoulders lightly, still sure to keep the majority of his weight off of Stiles, he began to suckle at the latter’s collar bone before moving up to his jaw.
“Ah.. Der…Ahh uh… uhh, Derek!” Each time his partner pushed against him, their cocks sliding together with the combo of sweat and precum, felt trickling down the side of his turgid member, Stiles lost his train of thought; starting and stopping again like a cautious new driver behind the wheel of a car, paranoid they might crash it if they move too fast.
“Do you…Oh God! …Do you have…” Stiles trailed off, too bashful to finish the rest of the sentence.
Even though he really had no idea why Derek had summoned him hear earlier, Stiles did have a condom in his pocket still now that he thought about it. He certainly knew it wouldn’t fit him — he was decent, but not huge — but, he would bet any money that the werewolf would fill it out nicely. The thought scared him when he thought of where his dick would then be going and he shuddered.
Derek chuckled lightly, after detaching his lips from the dip of the teen’s throat, and moved up to whisper in his ear.
“We won’t be needing that,” he said, and Stiles knew he probably ought to question this, but his brain was out of commission and there was a new sherif in town — namely the persistent little fucker currently digging into the muscle of Derek’s upper thigh.
Sliding wetly down the side of Stiles neck, over his collar, stopping to circle a nipple which immediately pebbled at the attention, the human could feel Derek’s tongue working its way downwards and it was making Stiles antsy. Reflexively, as the man neared the sensitive area where his cock was leaking embarrassingly, an angry pinkish colour against his belly, Stiles legs began to close. Derek was quick to place both hands on his thighs, kneeling between them, his face dangerously close to unchartered territory. Stiles closed his eyes, and for a moment he hoped that the age-old childhood trickery of ‘I don’t see you, you don’t see me’ would come into play right then.
“You ready?”
Derek’s thumbs were rubbing at small patches of pale skin. Stiles had thrown his arm over his face now.
“Not exactly,” he answered.
Derek smiled, and though Stiles could not see it, he could hear the amusement in his voice.
“You will be.”
Though the visual of Derek ducked down between his legs, a place no one had ever been or seen except him, until now, was most tempting, prying at the arm blocking his vision like a little child pestering it’s mother, Stiles couldn’t just yet bring himself to meet Derek’s gaze. He was afraid. Of course he was. He had good reason to be; and for the first time in years, he was opposed to the part of him that loved cracking jokes and being the centre of it all, simply wanting a giant hand to come out of the night sky and pluck him up. It’s not that Derek’s ministrations weren’t amazing, they were, but fear was beginning to consume him.
What if this went terrible, horribly wrong.
Stiles thoughts then became an instant sea of alphabet soup in mere seconds as he felt something hot against his most private of places. He darted up in an instant to see Derek’s hazel eyes looking right at him. Damn it! There was not looking away now. Stiles eyes almost rolled right out the back of his head when he felt the heat again, and now he knew what it was. The alpha’s mouth was just inches away from the entrance to his body, and his tongue was swiping back and forth over the top set of his teeth.
“Ever been here before?” he asked, and Derek turned his head to lick a small strip of saliva up the innermost part of Stiles thigh. Stiles shook his head violently, his eyes wide. He was finding it very hard to breathe now.
No one had been there before — not even him.
Derek’s grin after receiving this news should have been a little frightening, especially since Stiles had a clear view of his dangerously sharp teeth right now, which had pushed through the gums a while earlier when Mr. Wolf had tried to come out and play. But the fact that Derek was a werewolf surprisingly wasn’t what freaked him out most in that moment. What did was the act that the older man was about to perform next, though he was most certain he would like it, the idea of someone being down there was also kind of unnerving.
“You’re too tense, Stiles.” Stiles watched Derek intently as he reached for a small bottle sitting at the closest corner of the table which he hadn’t even noticed before now. There was a pearly, silver-coloured liquid inside. Reminding Stiles a bit of chrome. Derek didn’t uncork it, just moved it closer, and then scooped his arms back under the young man’s legs so once again his breathe was making Stiles clench involuntarily.
“I can fix that.”
Stiles swallowed deeply, his vision still locked on Derek, and then as the werewolf’s tongue plunged without warning into his hole, he couldn’t be more thankful for their location, deep in the woods, where it was unlikely anyone would hear him scream.
Without even thinking, Stiles hands made a beeline for Derek’s hair, gripping it tightly. At first he was worried he was pulling on it too hard, but that thought hardly stayed to say ‘Hello’ before he found himself willing Derek’s tongue to go deeper, pushing, tugging, urging, pulling and screaming. He’d jacked off many times, sure, what teenage boy hasn’t? But despite admitted curiosity as to what the sensation might be like, Stiles never tried to play with himself there.
In this moment he was regretting that fact.
Stiles breathing was so ragged that if they were to be interrupted right now, brought to an unexpected stop, as long as no one had walked in on them in the middle then one easily would have thought he already had sex. His face was red, from embarrassment, not exertion, and his body was slick with nervousness, not the aftermath of steamy passion, but it was doubtful that the average person would know the difference.
Scott would. Scott most definitely would.
“Oh God! …Oh my…Gaww-duh! Der… Derek… Stop!”
He didn’t want him to stop, but he certainly didn’t want to cum before Derek had the chance to get inside him. He could already feel the familiar tingle rising in his stomach. It would be embarrassing, but most of all, far from gratifying.
With one last gentle swirl of the wet muscle, then drag upwards and over Stiles balls which tightened momentarily at the brief contact, Derek sat up.
He looked to the glass bottle next to him, which Stiles had nearly nocked over with his squirming, and then back to the teen. Stiles was having a hard time deciding on where to look and slide up and down his body several times, stopping on his eyes for scarcely a second and then back down to his member, which looked even more incredible up close. Thick, lengthy, red. Spectacular and terrifying.
Stiles chest heaved. Derek grabbed for the lube blindly. He didn’t open it until he had received confirmation from Stiles in the form of a nod.
The cork bounced a few times and then rolled away from him as Derek pulled it from the bottle with his teeth and spat it towards the table. Stiles caught it before it fell over the edge and squeezed it nervously in his hands.
The liquid was thick and shimmery, and when it hit Derek’s fingers it slid effortlessly like oil through each digit. The alpha swirled it about on the pads of his index and middle fingers with aid of his thumb before pulling his body a bit closer to Stiles with his clean hand. He placed it flat against one of the human’s trembling thighs and as he caressed the skin their calmingly, he worked his slicked finger inside.
“Relax,” soothed Derek. The calming tone almost felt out of place coming from his lips. Stiles was so used to angry words and harsh insults, and they certainly didn’t come on angel’s wings. More like with the aggression of a rabid dog or bloodthirsty bat.
“Easy for you to say. You’re not the one with something up your ass,” replied Stiles somewhat aggravated and a little broken whilst Derek pushed passed the initial ring of muscle. “Well, unless you count the stick that I’d bet any money is always there.”
Derek curled his finger abruptly and Stiles breath hitched in his chest at the unexpected pang of pleasure it sent up the length of his spine.
“Everyone’s a virgin at one point, Stiles.” The older male raised an eyebrow before pulling out. Stiles whined at the loss of contact whilst processing what this meant. Coating two fingers instead of the one, Derek pressed into Stiles a second time and when the sounds of discomfort turned to pleasure, began a slow thrusting motion.
“Derek Hale… Ah… Bottomed?”
Derek gave a half nod in agreement before turning his attention back to the task of preparing the teen. He had snuck in a third one this time, and with the generous amount of lube he had applied and the temporary distraction, Stiles almost didn’t notice.
“Oh… fuck.. Ahh… You have to… you have to tell me who.”
“I really don’t.”
Stiles frowned, but it melted right off his face in no time flat when Derek’s other hand took the younger male’s cock in his hand and began to jack. The dual pleasure of both Derek’s fingers in his ass, and the rest stroking his weeping organ, had Stiles almost completely bowed off the table now. It wasn’t entirely a comfortable position, but he didn’t care.
This time when Derek removed his fingers, finishing with a sharp stab with four fingers to a bundle of nerves inside Stiles, Derek could hear the audible protest.
“You’re sure about this?” asked Derek.
Stiles pulled himself up with his elbows so he could look at the man, ignoring the scratch on his elbows from whatever was underneath the red sheet they lay on.
“Yeah,” he said, and even Stiles was a little surprised with how quickly that answer came.
“I do this and there’s no turning back.” Derek threw his clean hand back to ruffle through his hair. With his legs spread the way they were, his cock on perfect display, Stiles was having a hell of a time concentrating on Derek’s words. He desperately wanted to get his hands on him, to run his tongue all over the swollen head, but the teen wanted it inside him more. He needed it. Literally.
“If I do this. You are mine, Stiles.”
The human’s eyes went a little wider at this, even though he knew full well that that might be the case. It was just scarier when he gave it more thought. Wolves mate for life, he remembered reading somewhere, and Derek certainly did not yet have a mate. Derek's a werewolf, so it's not like the rule was exactly solid. He was part wolf. Did it mean all those others were just sex? What made Stiles so special that Derek would think he was mate material? Stiles had always thought his crush on the man was one-sided though, so there was every doubt in his mind that unless within his own fantasies, Derek would reject him soon after the deed was done. Mating never really came up. It didn’t seem possible. Though now that Derek said it, it felt surprisingly real.
If this went well, and Stiles had a wonderful feeling it would, he wouldn’t be able to get rid of Derek.
A second realization came that he didn’t want to.
Leaning forward awkwardly, finding it to be nowhere near as simple a task as expected to reach for Derek with just one arm, Stiles fingers brushed over the other man’s knuckles. The man’s hand had come to lay flat against the table next to Stiles side, when he had leant closer.
The night air rushed through the broken down building and surrounded them again, and Stiles shivered a little as it cooled the fluid which Derek had used to work him open. Derek seemed surprisingly calm, even though on the inside there was a caged beast thrashing against the bars, as he waited for Stiles answer. Derek tried to ignore the delicious spike in his middle as his cock accidentally brushed against Stiles’. They moaned in almost unison.
“Derek,” Stiles was looking right into the wolf’s eyes, and they were already a little glassy. “I want you to do this.”
In one swift motion, Derek dragged Stiles body closer to him, wrinkling the fabric underneath them, and immediately directed his dick to the human’s slick hole. Stiles watched carefully, and there was fear there but also a great deal of want. Derek focussed on that as he reached down to guide himself to his target, making sure the entry would be as smooth and steady as possible.
“This will hurt,” Derek warned, deciding it would be better to tell Stiles ahead of time rather than just barrelling in and hoping for the best. “You need to relax.”
Stiles made a sound of agreement and lowered himself back to the table. His head made a slight clunk sound as he hit it and he cursed under his breath.
Derek wasn’t wrong. Of course he wasn't. The pain was intense to start and Stiles found himself scrunching his eyes shut so tight he thought they just forge closed — as if that would help. The burn, despite Derek’s careful preparation was immense and the younger male’s toes curled as the pain shot through him like electricity through a power cord. He screamed as he felt every inch of the slow slide inside him, and he almost yelled for the brunette to pull out.
At the halfway mark, Derek stopped pushing, and Stiles suddenly felt the alpha’s hands on his sides again, rubbing up and down, easing his eyes open.
“St-iles,” he groaned, it sounded like he had to force the word from his lips. Perhaps he was hurting too.
Stiles was breathing fast again, like he’d just run a race or jumped over a hundred hurdles spaced way too close together. The worst wasn’t over, not yet. Derek wasn’t even to home plate yet. When stole a glance up at Derek, he looked like he was about to explode, and there were sharp pricks making his long talons even more known against Stiles’ flesh.
“Take deep breaths. Stop clenching.”
Siles did as he was told, and the pain did fortunately ease a bit, but there was still discomfort. Perhaps because Derek still had a ways to go and the real fun hadn’t even begun yet. Wait. Fun. Apart from the earlier make out session, Stiles wasn’t sure if what was happening now could be classified as that.
Derek’s hands were a little rough as they moved against Stiles skin, trying to calm him further, but the slight scratch gave the younger male something to concentrate on rather than the pressure inside him. Speaking of pressure. Stiles unfolded one of his arms from under his head and slid it down his front until it reached his cock and then he gripped it tightly. He spasmed a bit at the mere touch as he was so hard it was almost painful, but it held his attention and he was able to relax enough to loosen up.
Taking Stiles much more pleasant expression to mean he was ready, Derek pushed the rest of the way in as swiftly as possible to avoid drawing out the pain any longer. The burn was still there, but when the alpha had buried himself completely to the hilt and slammed hard against a particular sensitive bundle of nerves, Stiles cried out loud.
“Jesus! Oh my …Ohh.”
Derek gave Stiles time to adjusted to the impossible fullness, simply grinding against him for a moment or two until again he could see the tell-tale signs of pleasure of the man’s face, and then pulled back slowly. He didn’t go far the first time, worried he might have hurt Stiles, but then his eyes flew open again after the shallow thrust and Derek knew the pain had been buried and another feeling had taken control.
“Derek, just ..go …go go go… Now!”
He pulled out almost all the way this time, to the point where he nearly had exited Stiles body completely, just the head of his cock keeping him wide and open for him, then Derek gave an experimental thrust. Testing the speed to see if it was too much, just right, or not enough.
Stiles hand, which was moving lazily on his cock, was a blur now.
“Slow down,” said Derek. At this rate Stiles would blow before they had barely got going. It also looked like he was about to have an aneurism or something, and Derek wondered if Stiles was always this enthusiastic with his wanking.
Derek’s rhythm soon quickened to the pain where Stiles legs were trembling and Derek was starting to lose feeling in his thighs from the way he was positioned. He stopped thrusting with all the control he could muster, cutting down the speed but still grinding as if some unseen force was denying him the right to stop all movement, and then moved back to the edge of the table before stepping off one leg at a time.
“Oh god… uh..uhh Derek… wh-what are you ..ohhh!”
The jostling was sending shockwaves through Stiles body, his no longer virginal body, and each one felt twenty times more intense than it probably should have. This was his first time after all. He’d never done this before. As much as he hoped each time after this would go just the same, Stiles relished in each surge as the feeling that after this point, sex would only go down hill, became ever present. Fucking just anyone surely wouldn’t be as enjoyable as fucking a werewolf.
Not bothering to pull out, Derek held out his hand for Stiles to grab.
“Here,” he said roughly, his voice low in is throat, giving Stiles chills for a whole different reason.
Stiles took it without question, well not vocal at least. His expression seemed to be asking a whole lot at once.
Derek didn’t say anything more, he just smiled and pulled Stiles up to an almost seated position. The younger male winced as he was jerked closer, cock still firmly planted in his ass, and when Derek wrapped his arms around Stiles’ middle, he did the same but around the other male’s neck.
The angled changed completely, and definitely not in a bad way. Stiles mouth fell open as Derek gripped him tightly around his waist. He lifted him slightly off his dick like he weighed nothing at all before slamming him back down again and repeating over and over again until establishing a steady pattern.
Stiles wouldn’t say he was necessarily fit per se, but he wasn’t unhealthy either. He clenched the muscles in his abdomen as tight as he could, and using the muscle he did have in his arms to aid Derek, he lifted himself upwards. Stiles could feel the ripples in the alpha’s muscles as he continued to bounce up and down, spearing himself on his first ever cock, and his own rubbed against Derek’s abs leaving a smear in its wake, disrupted every time he moved.
“Derek, Derek, Derek.” the werewolf’s name fell as a mantra from Stiles lips, and the aforementioned knew the teen was close. He was honestly surprised Stiles had made it this long, to be honest.
Stiles was the one to come first, expectedly. He could feel it dripping down his own front and surely it was all over Derek’s as well. Though he couldn’t see it, the visual in his minds eye was spectacular. Normally the first thing he would do was reaching for the warm cloth, but Stiles felt oddly content where he was.
Since he didn’t see one around and Derek showed no signs of slowing, still chasing his own release, Stiles simple smiled into the older male’s neck and held on for the ride, letting out faint groans and pleasant moans as the shards of pleasure from his own orgasm spread out within him.
As Stiles waited for Derek to finish, a dull pulse within his body where the man’s cock was still thudding up into him, he realized that the aftereffect of his own climax wasn’t the only thing spreading. The pulse grew stronger and stronger, like the loud beating of a heart when you pressed your face to someone’s chest — it’s solid and violent, and just how he thought Derek’s might be like right now if he had the space to test that theory — and soon any pleasure remaining in Stiles was gone in a flash.
The pain was back, intermixed, just like it had never left him.
“Oh .. Oh my go— Oh my…! Derek!”
Derek said nothing, just kept on going, moving his hips at a lightening speed and gripping Stiles ass cheeks so hard the latter full expected there would be quite healthy bruises there in the morning. The thrusts felt good, the slick feel of Derek’s dick sliding against his insides made him lose his breath, but the strike to his prostate was beginning to become unbearable. Fortunately he didn’t have to much longer as Derek stilled suddenly.
He laid Stiles back down on the table as gently as he could but didn’t pull out.
“Wha-what is th-th …Ohmygod! What is that?” Stiles felt a immediate heat in his core and Derek let out a deep growling sound as he threw back his head and came.
“Woah! Dude!” Stiles wasn’t sure what to expect. He’d never done this before. But after several minutes had passed, it was clear to him that this wasn’t something that normally happened.
Derek opened his eyes slowly, and his breathing gradually slowed to a normal speed. There were scratch marks on Stiles skin, nothing deep enough to turn him or anything, but he was sure to check anyway for blood. Nothing. Just angry pink lines.
“Sorry,” he said softly, and Stiles wasn’t even sure if sound had actually come out, he just recognized the movement on Derek’s lips. He’d used it enough times himself o recognize it anywhere.
Stiles made a face as if to say, What the fuck!, his eyes wide and his mouth hanging slack as if he wanted to say something but couldn’t exactly figure out how to put it into words. The throbbing inside of him was still ongoing, and after Stiles discovered trying to pull back himself only caused shoots of pain to spark off every which way, that it best not to move.
“As much as I’m… en-enjoying the closeness, and all, Derek… I think you could pr… uh…prrobably pull out now,” the teen said around winces of pain and the odd gasp of pleasure. He wasn’t sure what to feel.
“I can’t,” came the reply.
“You can’t. Okay, you… can’t. Wuh, wuh… wuh-why can’t you?”
“It’s called a knot, Stiles.”
“A knot? That sounds alarmingly… permanent.”
Derek nodded.
“It swells up after intercourse to ensure insemination with the females. Stops them from running away. I have no control of it, I’m sorry,” Derek explained in the best way he could, to which Stiles looked almost horrified.
“Isn’t that something you should have …oh, god… something you should have warned me about?”
Derek nodded again.
“I should have, yes. I just, well … obviously you’re not a female so I didn’t expect it to be an issue.”
Stiles rolled his eyes.
“How long does this … ‘insemination’ process usually last?”
Derek turned his head to face the wall where an analog clock was ticking loudly. In reality it probably wasn’t all that loud, but to his heightened senses it was as annoying in this moment as a bee buzzing about his ear.
“How long, Derek?”
“Half an hour. Maybe more. Do you have somewhere to be?”
Stiles, for once, was speechless.
Not anymore.